Trail Running calendar near Highfield-Cascade 2026-2027

A measured *100-mile* loop through the Massanutten Mountains and Shenandoah River Valley with varied terrain, 14,000 feet of gain and 14 climbs. The volunteer-run event offers a 24 hour cutoff for the silver buckle.

A 45th annual five-mile out-and-back on the C&O Canal Towpath in Williamsport, MD, on June 6, 2026. Chip timing, a technical race shirt, and age-group and overall awards are part of the event.

Awesum Possum Lake Trail Adventure at Opossum Lake Park offers a 6 mile obstacle course, a 4 mile run, and a 4 mile walk. The mixed-terrain course follows the Anglers Access Trail, uses chip timing, and benefits the Friends of Opossum Lake..

Event Overview The Fauquier Education Farm 5K and Fun Run is a fundraising event for the Fauquier Education Farm, a 501(c)(3) organization. The organization's mission is to advance agriculture through education and best practice farming. It..

A trail race on June 19 at Button Farm in Germantown offering 6k and 12k distances around the Schaeffer Farm Trails. The event counts toward series scoring, includes chip timing, shirts and medals, and offers a virtual option.

A rugged out and back on the Catoctin Blue Trail near Frederick, MD offering a 50K and a 25K Half Cat, with rocky singletrack, shaded forest, stream crossings, three staffed aid stations, and mandatory carried hydration.

Run the scenic Puso 10K on the flat, gravel C&O Canal path in Georgetown, Washington DC. This chip-timed event benefits the PUSO Foundation and awards top finishers. All participants receive a finisher's medal and tech shirt.

Trail 5K and 10K at Seneca Creek State Park in Gaithersburg, MD featuring singletrack trails, lake views, aid stations, post race food, and a charity partner Interfaith Works.

This cross-country event takes place at the Agricultural History Farm Park in Derwood, Maryland. It's part of a free series for members, with paid registration available for non-members and a youth discount.

A free Forrest Gump themed fun run on Lakeside Loop in Owings Mills offering a full 4.4 mile loop or a 1 mile out-and-back option, meeting at New Town Village Center with themed attire suggested.

A point to point 100 kilometer trail ultramarathon across the Ridge and Valley region of southern Pennsylvania, covering Juniata River watershed and Rothrock State Forest. Organized by the Eastern States Trail-Endurance Alliance on July 11..

A summer trail race at Gunpowder State Park on July 12, 2026, listed as 7 miles with the course described as about 8 miles and crossing county lines. The route features rolling hills, water crossings and varied terrain, and field size is li..

Endless Summer 6 hour Run is a timed six hour event at Greenbury Point Nature Center in Annapolis on July 18, 2026. It is listed on the Annapolis Striders race calendar.

A cross country 5k and 10k at 868 Estate Vineyards with chip timing, a virtual option, race awards, and a postrace glass of wine for participants.

Trail race at Button Farm Living History Center in Germantown on July 25, 2026, offering 5K and 10K courses on maintained single track with stream crossings and some rocky, rooty sections.

Run a festive half marathon or 5K on the scenic C&O Canal path in Georgetown. The event benefits the Purple Heart Foundation and counts towards year-long running series points. Participants receive a medal, tech shirt, and chip timing.

Trail races at Little Bennett Regional Park on August 1, 2026 offer 5K and 10K singletrack courses with hills, stream-side sections, aid stations and post race food.

Run a 5k, 10k, or half marathon on the scenic trail loops of the Third Winchester Battlefield. The event includes chip timing, a finisher's medal, and supports Operation Enduring Warrior. Walkers are welcome, and participation counts toward..

A trail race in Elkridge, MD on August 15, 2026 offering 25K and 50K options on rolling single track with river crossings, aid stations with real food, and an on-site finish area with pavilions and refreshments.

Run on the flat, scenic dirt trails of Leopold's Preserve in this 5k and 10k event. Participants receive a medal, shirt, and chip timing, with points counting towards several annual series. A virtual race option is also available.